


Shaking Hands

by CR Noble (erudite12)



Category: Supernatural
Genre: After care, Anal Fingering, Anal Sex, Anna is a good friend, Biting, Bondage fantasy, Chastity, Coming Untouched, Dom!Cas, Dom!Michael, Drinking, Escort!Michael, F/F, F/M, Facial, Feels, Frottage, Light Bondage, M/M, Masturbation, Michael talks about his feelings, Multi, Objectification, Prostitution, Public Sex, Rimming, Rom-Coms, Rough Sex, Spanking, Sub!Crowley - Freeform, Sub!jimmy, Teasing, Threesome, Top!Cas, Top!Michael, Twincest, Unprotected Sex, Wedding Reception, begging fantasy, blowjob, bottom!Crowley - Freeform, bottom!Michael, bottom!jimmy, dom/sub dynamic, escort AU, girls night, lucifer is not a bad guy, michael and lucifer have a good relationship, sub!Michael, switch!Michael, this fic is going to have so many tags by the time I am done here, vers!Michael, wine ice cream and movies, wrap it before you tap it kids
Language: English
Status: In-Progress
Published: 2019-07-31
Updated: 2019-09-06
Packaged: 2020-07-09 08:48:24
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 19,103
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19884877
Author URL: https://archiveofourown.org/users/erudite12/pseuds/CR%20Noble
Summary: At 28 years old, Michael Milton loves his life. What’s not to love? He’s attractive, rich, smart, and he has a lot of sex. It kinda comes with the territory, and Michael has no plans on changing any time soon. Or ever. Monogamy is not for him. And if he makes a little (or a lot) of money off of it? So much the better.When he falls in love along the way, all he can do is hope Crowley understands.





	1. Chapter 1

**Author's Note:**

> Woohoo, there's going to be _so many rare pairs_ , I hope you guys enjoy reading them as much as I enjoyed writing them!
> 
> This series is written to fill squares for SPN Kink Bingo 2019 (there is one chapter with no square though haha)

**Notes for the Chapter:**

> A huge thank you to [Imoshen](https://archiveofourown.org/users/Imoshen/pseuds/Imoshen) for beta reading this chapter for me :D
> 
> I really appreciate it because it can be such a pain to find betas for rare pairs!
> 
> Tags for this chapter: Michael/Cas, escort!Michael, top!Cas, bottom!Michael, rimming, biting, Dom/sub dynamic, dom!cas, sub!michael, spanking, anal sex, rough sex, aftercare, escort au, prostitution
> 
> Tags for the fic as a whole will be updated as I draft each chapter into AO3, and chapter-specific tags will be included in the notes for that chapter :D
> 
> Chapter 1 fills the Biting square for my Kink Bingo card

“Thank you,” Michael said, taking two tumblers of scotch from the bartender and turning back toward the table where he’d left Castiel. An amused smirk crossed his face when he saw that Cas had been cornered by a petite redhead in a long, backless ball gown. Judging from the mild panic on Castiel’s face, she was flirting with him shamelessly.

Michael would have thought Cas would be used to it by now. He was gorgeous, after all, with his piercing blue eyes, permanent five o’clock shadow, and dark, just-fucked hair. And, even if it wasn’t really intentional on Cas’s part, he had worn _the_ jacket. The dark blue made his eyes stand out even more than usual, and the cut accentuated his muscular torso exquisitely. On top of the fact that he was beautiful, Cas was smart, wealthy, philanthropic, and mostly single. 

He was also extraordinarily gay. The small woman twisting a long, red curl between her fingers either didn't know or thought herself capable of changing his mind.

Of course, that exact situation was part of the reason why Castiel had Michael accompany him to events like this one. That and the fact that Cas was awkward and asocial at the best of times. Michael, on the other hand, was a social butterfly. He was self-aware and adaptable, good at handling people, and he thrived on the attention.

His social skills were at least half of the reason he was so sought after in his profession.

“Castiel,” Michael said with a smile, setting one of the tumblers on the table in front of his companion. “I hope you aren’t planning to abandon me in favor of this gorgeous creature.” Cas looked up as Michael bent to press a kiss to his cheek.

“I would never,” Cas replied. He smiled gratefully and turned back to the redhead, looking a little more confident. “This is my date. Michael.”

She looked over at Michael, and he stood up straight and watched as her gaze slowly traveled from his neatly combed black hair to his blue eyes, from the sharp line of his jaw to the perfectly tailored Armani suit that managed to show off the broadness of his shoulders and the narrowness of his waist in a very intentional way. Michael was well aware of how attractive he was, and he made every effort to play it up.

The woman’s voice was sultry, with a foreign lilt and the languorous drawl of someone that was born rich and never had to work a day in her life. “Well, don’t you two make quite the matched pair.”

She was older than him; she looked like she was in her early forties, but she was probably closer to fifty. Her natural beauty was evident, even under the bright red lipstick and the metallic green eyeshadow that only served to make her eyes seem that much brighter. She carried herself with the kind of grace and confidence that other people would kill for, and she _knew_ it.

But Michael was there for Castiel.

“I’m spending the night here at the hotel if you gentlemen would like some company,” she offered smoothly, raising an eyebrow suggestively.

The corner Michael’s mouth drew up into a lazy smirk. Any other time he would have taken her up on that. “As much as I appreciate the offer, I’ve got my hands full with this one.” He lowered himself into his chair and took one of Cas’s hands in his. “Both hands… _very_ full,” he finished with a wink at the woman. From the corner of his eye, Michael saw a crimson blush spreading from Cas’s cheek down toward his neck.

“I’m in room 334 if you change your mind.” She smiled knowingly, letting her eyes linger a moment longer before turning away. She swayed her hips as she walked, her long dress swishing against the floor.

Castiel smacked his arm lightly but mostly just looked relieved that she was gone. “You’re going to pay for that,” he said, a playful twinkle in his blue eyes.

Michael laughed softly and brought Cas’s hand up to brush a kiss against his knuckles. “Is that a promise, Mr. Novak?”

“Now you’re just asking for trouble.” His voice was teasing, but Michael knew he meant every word. Castiel wasn't one to say things extraneously.

Of course, Michael already knew he was pushing his luck. The knowledge had never stopped him before, and it certainly wouldn’t stop him now. He stayed at Castiel’s side for the rest of the event, more than happy to help him wade through the social pond. He kept Cas's hand in his for most of the evening as he deftly guided him through exactly the type of dry, superficial conversation that Michael loved—because it meant he didn’t have to have anything _real_ to say—and Cas hated. 

As usual, Michael learned much more about the people attending the charity ball than they learned about him. Castiel appeared drained when they finally stepped into the empty elevator that would take them up to their hotel room.

Castiel knew much more about Michael than most of the people in his life, and even that really wasn't much. He and Cas had known each other for several years, and Michael actually cared for him very much. Their time together, no matter how much or little, was something Michael enjoyed very much. Castiel seemed to feel the same way, even if he was just as tight-lipped about his personal life as Michael was.

The elevator doors dinged open on their floor, and Michael threaded his arm through Cas’s, linking their elbows as they stepped off and walked down the hall to the door with ‘423’ printed on it. Michael swiped the key card and pushed the door so it swung inward. “After you, Cas.”

Waiting a moment for Castiel to pass over the threshold, Michael followed him. As soon as the door clicked shut behind him, his back was pressed against it and he was pinned between the cold wood and the hard muscle of Cas’s chest.

Cas’s breath was hot against Michael’s ear when he whispered, “I think you’re going to have much more than just your hands full tonight.” Then his mouth claimed Michael’s, hard and demanding, tongue prodding for entrance. 

Michael parted his lips with a throaty groan, wrapping one arm around Cas’s waist and threading the fingers of his other hand into Cas’s soft hair to pull him closer. Even through the layers of his jacket and shirt, Michael could feel the hot trail of Cas’s hands running up his sides, and he desperately wanted to feel them against his skin.

Tilting his head to deepen the kiss, Michael gave as good as he got, a battle for dominance in the hot, slick slide of his tongue against Cas’s. Michael was breathless when Cas pulled away and stared at him with lust-dark blue eyes that would probably burn holes in his flesh if their gaze rested on one spot for too long. With deft fingers, he unbuttoned Cas’s jacket, holding his gaze as he slid his hands up and pushed the jacket off of Cas’s shoulders. It slipped down Cas’s arms and fell to the floor behind him, and Michael reached for the blue tie.

Cas caught Michael’s hands and shook his head. “You first,” Cas said as he reached for the button of Michael’s jacket. Michael let his arms fall to his sides as Cas opened the blazer, almost popping the button off in his haste.

“Hey,” Michael chided as he shrugged it off, arching off the door and pressing his hips against Cas to let it fall. Cas’s cock was already swelling, half-hard against Michael and he felt the answering twitch of arousal in his own. “Watch yourself, this is a six thousand dollar suit.”

Cas laughed and loosened the knot of Michael’s tie, pulling the tail out and sliding it through his collar so fast it came free with a sharp snap. Dropping it, Cas grabbed fistfuls of the panels of Michael’s shirt and tore it open, sending the buttons flying as he exposed the tanned flesh beneath it. Michael winced, about to complain about the damage to his very expensive shirt, but Cas spoke first. “I’ll buy you a new one.”

Michael didn’t really care about the shirt, it wasn’t like he didn’t have the money to replace it. And truth be told, the display of dominance was incredibly hot. Especially with the way Cas’s hands turned gentle against Michael’s skin, slowly slipping the torn shirt over his shoulders and down his arms, the touch leaving a trail of goosebumps following it. Michael’s heart raced and his cock strained against his pants, the soft silk of his boxers caressing the head every time Cas did something that made it twitch.

Cas stepped back for a moment, letting out a low hum of approval and palming himself as he caught his lower lip between his teeth and raked his eyes up and down Michael’s frame. “You are a work of art, Michael.”

“Thank you,” Michael breathed. Cas’s eyes met his and one eyebrow lifted, admonishing Michael without a word. His heart skipped a beat and his dick throbbed. He licked his suddenly very dry lips. “Thank you, Mr. Novak.”

Taking both of Michael’s hands in his, Cas stepped forward and slowly lifted Michael’s arms above his head. “Very good.” His fingers trailed down Michael’s arms, barely making contact. “Keep them up and turn around for me.”

Michael spun carefully and Cas pulled him so that his back was flush against the silk of Cas’s shirt. He fought the urge to reach back and tangle his hands in Cas’s hair and stretched his fingers toward the ceiling instead. 

“Is this okay?” Cas asked, palms gliding up Michael’s abs. “You’re not getting too uncomfortable?”

“I’m good, Mr. Novak,” Michael replied, his voice breaking just a little as Cas thumbed over his hardened, sensitive nipples. “I’ll let you know if I need to put my arms down.” His eyes fluttered shut as Cas pressed full, soft lips to his shoulder.

“Such a good boy,” Cas said, pushing his hips into Michael so he could feel the hard, thick length of him press against the cleft of his ass. “You were not so good earlier when you spoke to that woman. Remind me what that naughty thing I promised you would pay for was.” Cas put a hand between his shoulder blades, easing him forward until his forearms rested against the door. 

Michael swallowed harshly as Cas worked his belt buckle loose. “I told her that I would have both hands very full with you tonight.” Leather whispered against fabric as his belt was pulled loose from the loops on his pants. Cas’s hand was so close to his cock, it took almost every ounce of willpower Michael possessed not to move his hips and seek the relief of friction he wanted so badly.

Cas busied his fingers with the button and zipper of Michael’s pants. “And why did you do that?”

“I wan—” Michael groaned as his dick sprang free from the waistband of his boxers, slapping his stomach and bobbing between his legs. Cas pulled his pants and boxers down his legs achingly slowly. “I wanted to make you blush, Mr. Novak.”

Cas’s hand came down hard across the left cheek of his bare ass, and Michael yelped at the harsh sting that made precum bead at the tip of his cock. “So, you thought it appropriate to embarrass me?” Cas asked, rubbing the pain away with slow circles.

“No, Mr. Novak,” Michael said, voice low and thick. Another hard smack, this time to the other cheek, and he bit his lip with a moan. “It’s just that you’re beautiful when you blush like that.” Cas hummed, the sound deep in his throat, and smacked Michael four more times. His ass was hot from the impacts, and he imagined it was at least as red as Cas’s face had been in the ballroom earlier.

“I think you owe me an apology.” Cas kneaded his cheeks in his hands. “Don’t you agree?”

Michael nodded; Cas’s breath felt cool against his heated skin. “Yes. I’m sorry for embarrassing you, Mr. Novak.”

“I know you are,” Cas crooned. “Are you still okay?”

Michael’s arms and shoulders were a little sore from bracing himself against the door as Cas spanked him, but it wasn’t too bad. His cock was aching, needy for touch, but he this wasn’t his first rodeo and it certainly wasn’t bad enough to stop. “Yeah, I’m alright.” Teeth bit harshly into one fleshy cheek and Michael cried out. Fuck, Cas knew how to drive him crazy. “Not too hard, Cas. No marks.”

He replaced his teeth with the flat of his tongue, lapping over the bite once. “I know the rules, Michael. I haven’t forgotten.” Cas didn’t speak again and then his tongue ran up the cleft of Michael’s ass, from his perineum to his back, and Michael forgot how to form words. Cas spread Michael's cheeks and circled his rim with his tongue, teasing him open.

Michael’s forehead hit the door, resting there as Cas buried his face in Michael’s ass, alternating between sucking at his hole and lapping at it. As Cas’s tongue pushed past the ring of muscle, Michael’s thighs shook with the effort of being still, and he whimpered and moaned and wished like hell Cas would touch his dick. 

Cas, of course, did no such thing. He just worked Michael’s hole relentlessly with his tongue.

“Please, Mr. Novak,” Michael groaned. He felt like he might explode; he needed more.

Pulling away, Cas asked, “Please, what, Michael?” His hands gently massaged the back of Michael’s thighs as he waited for an answer. His voice was hardly more than a rasp, and Michael could tell Cas was just as far gone as he was. “Tell me what you need.”

Michael took a moment to catch his breath and feel the tingling in his shoulders. “I need to lower my arms.” He panted for another moment. “And I really need you to fuck me.”

There was a shuffle of fabric behind him, and Michael assumed Cas was standing up. “You may lower your arms.”

Letting his arms fall to his sides, Michael leaned against the door and shook them out a bit, until the pins and needles were gone from his shoulders. “I’m okay now,” he said finally, putting his hands against the door again for support, though not so high this time. “Now, for the love of God, will you _please_ fuck me properly?”

There was a snap, and after a moment filled with the sound of Michael’s heart pounding violently against his ribs and his heavy, erratic breathing, he felt the slick head of Cas’s thick cock pressing against his hole, pushing slowly past the rim. The deep rumble of Cas’s needy groan as he gripped Michael’s hip with one hand and buried his full length in Michael’s ass reverberated in his ear. 

Michael moaned at the sensation of being stretched and filled, the burn of it a pleasure just bordering on the line of pain. Cas’s free hand glided up the sweat-sheened skin covering Michael’s spine to fist in his hair. The moments Cas waited to let Michael adjust to his substantial size felt like an eternity.

Then Cas pulled out and thrust harshly into Michael, making him cry out. “You make such pretty noises for me, Michael,” Cas said, fucking him hard and fast as he pulled Michael’s hair and made his back arch. A litany of praise streamed from him as he wantonly pounded into Michael.

How the hell Cas could still manage words, Michael wasn’t sure. The brush of his cock against Michael’s prostate drove any fine motor skills Michael had left out of his body, and the room was filled with the sharp slap of skin against skin and grunts and moans of ecstasy.

“Cas, please,” Michael begged, barely more than a whisper. “I need—”

Fingertips dug into his hip as Cas rasped breathlessly, “Touch yourself, Michael. Come for me.”

Michael took his cock in his hand gratefully and stroked himself as hard and fast as Cas fucked him. He was so close that it took only moments for him to cry out his release, coming in long, pulsing spurts that splattered and dripped down the surface of the door. Tears of relief and ecstasy sprang to his eyes as he worked himself through the intense orgasm.

Cas wasn’t far behind him, stilling as he filled Michael to the brim, painting his insides in hot strips. He rested his forehead on Michael’s shoulder, and they stood there like that—leaning against the door and breathing raggedly—for a long moment.

“I can’t stand anymore,” Michael said when he caught his breath. He was tired and his legs felt like jello. He felt Cas nodding against his shoulder, and he winced a little as Cas pulled his softening cock out of Michael’s overstimulated hole.

Cas turned Michael around to face him and dropped a chaste, tender kiss to his lips. “Come lie down. I’ll get you some water and clean us up.” Cas helped Michael over to the bed, laying him on his side atop a towel Michael assumed Cas had placed there earlier. Then he disappeared into the bathroom.

Michael was nearly asleep when Cas returned with a cup of water and a warm washcloth. He grinned goofily as Cas used the washcloth to clean up their collective mess, the warmth of it soothing against Michael’s sensitive skin. “You’re basically the king of aftercare, you know.”

Cas chuckled and helped Michael get under the blankets, then handed him the water. “Drink this. The whole thing. I’m going to finish cleaning up and I’ll be right back.”

Michael nodded and sipped at the water, waiting for Cas to come to bed. The cup was empty, and Michael was drifting off when the bed dipped under Cas’s weight. He wiggled on the mattress until he was flush against Cas’s and then rested his head on Cas’s chest and wrapped an arm around him. “Night, Cas.”

“Goodnight, Michael.”

* * *

Cas’s alarm woke them both when it went off at 7:30—far too early, if Michael did say so himself—and they both rolled out of bed and got dressed. Michael dug into his duffel and pulled out a pair of dark blue jeans and a black t-shirt, and put them on before sitting on the edge of the bed, waiting for Cas to finish in the bathroom. He’d take a shower at home before going into the office for the day.

Cas was towel drying his hair when he stepped back into the bedroom with a smile. “Morning,” he said cheerily. He walked over to his own suitcase and unzipped the front of it, reaching in and producing a thick stack of bills. “I know how busy you are and I don’t want to keep you.” He held the stack out to Michael.

“Cas, you know I’ve always got time to spare for you,” he replied, taking the cash with an affectionate smile.

Cas nodded. “There’s nine thousand there. The extra should cover the shirt I ruined.”

Michael protested, “You don’t have to replace that, really. I’ve got plenty of them.” He counted six hundred-dollar bills from the top of the stack and held them out to Cas.

“Keep it,” Cas said, walking over to where Michael sat on the edge of the bed and bending down to kiss him. “Trust me, you are more than worth the money.”

Knowing Cas wouldn’t take the extra cash back, Michael smiled and stood. “You’re too good to me. I’ll see you next time, okay?” Grabbing the duffel and throwing it over his shoulder, Michael said his farewells and headed out the door.

Castiel Novak was, by far, Michael’s favorite client. Of course, he enjoyed the time he spent with all of them, but Cas was special. If they had met under different circumstances, or in a different life, Michael might have loved him much more deeply. Even given the nature of their relationship, Michael couldn't deny that his feelings for Cas were much more than what an escort felt for his client. 

Michael wasn't willing to give up his job, not even for Castiel. He loved it. It wasn't about the fancy parties or the mind-blowing sex, though he certainly wouldn't deny those were perks. He had a knack for figuring out what his clients needed from him on a social and emotional level, and giving people something they needed made Michael feel good. It gave him purpose.

Getting handed nine thousand dollar stacks of cash helped, of course. But the only reason Michael could charge such a high fee was that he was good at what he did. In every aspect. Some might think him arrogant, but he just knew his value and had no problem making sure the people around him knew it, too. He was an excellent conversationalist, lover, and social partner. And he was smart enough to hold his own in any situation.

His time was absolutely worth the exorbitant amount of money people paid for it. Michael hit the unlock button on his key fob and slid into the driver’s seat of the black Tesla, shutting the door and buckling his seat belt before starting the car and heading home.

**Notes for the Chapter:**

> Did you enjoy this as much as I did? Because hot damn, Cas and Michael were ridiculously hot together!  
>  _How did I never think of this before?_
> 
> If you liked it, leave a kudos or comment (or both), and feel free to come yell at me on Tumblr. [@cr-noble-writes](https://cr-noble-writes.tumblr.com/)
> 
> If you want to receive updates on new chapters posting for Shaking Hands (or anything else I might happen to write), please subscribe, or head on over to my [Add Yourself Taglist](https://docs.google.com/document/d/15YTDA9uOfe28KaUDbB8MzYqcLn2JcYpmo4pu6S6qFDg/edit?usp=sharing) and drop your Tumblr URL


	2. Chapter 2

**Summary for the Chapter:**

> Crowley's usually the most powerful, confident person in a room. But everything Michael does from the moment he shows up puts Crowley on his heels. It's a good thing Crowley is open to new experiences because he's never seen anyone like Michael before.

**Notes for the Chapter:**

> Hello! Welcome to chapter 2!
> 
> This fic has so far gotten much more response than I thought it would, given that its basically just a grand amalgamation of rare pairs, with an endgame rare pair. 
> 
> It's really exciting to see that people are enjoying it! And I appreciate the hell out of everyone who has decided to read it!
> 
> A big thanks to [Hollyblue2](https://archiveofourown.org/users/hollyblue2/pseuds/hollyblue2) and [Fangirlingtodeath513](https://archiveofourown.org/users/fangirlingtodeath513/pseuds/fangirlingtodeath513) for beta reading this chapter even though this isn't your pairing <3 y'all are a gift!
> 
> This chapter fills the Dom/sub square on my kink bingo card.
> 
> Chapter tags: Michael/Crowley, Dom/sub dynamic, top!michael, bottom!crowley, dom!michael, sub!crowley, frottage, teasing, blowjob, anal fingering, anal sex

“Would you mind answering that, Anthony?” Crowley asked—ordered, really—when he heard the knock on the door. He wasn’t exactly giving his personal assistant a choice in the matter. Glorified bloody secretary wasn’t much use for anything else anyway. As the unfashionable, scrawny man’s cheap-soled shoes clicked on his way to the door, Crowley opened the top drawer of the dresser and went about the task of choosing a tie. Far be it from him to deny how important proper attire and accessory choices were in business. It had taken him some time to settle on the black suit with gray pinstripes so dark, one might miss them if they didn’t know to look for them, and a charcoal gray silk shirt.

But the tie was important. One could tell a lot about a man by his choice of tie. The right one would be a subtle display of confidence and power. Crowley pulled out a deep blue brocade and then stepped in front of the mirror and started to tie it.

“Mr. Macleod?” Crowley didn’t recognize the voice. It was young, male, deep and confident. He turned to face its source. “I’m Michael Milton. You requested my company for the evening?”

Crowley’s brain stuttered for a moment—something he was entirely unused to—as he took in his dinner guest. Michael had artfully tousled black hair, startlingly blue eyes, and a stubble covered jaw that belonged on a Greek hero. He wore a collarless, navy blue jacket that hugged his athletic frame over a fitted white dress shirt and a navy houndstooth bowtie. Crowley generally thought bowties were a bit ridiculous if he wasn’t wearing a tux, but seeing one on Michael, he might understand the appeal. The slim fit slacks matched the jacket, and the brown leather dress shoes on his feet may actually have been nicer than any of the shoes in Crowley’s closet. A slow smirk crossed the young man’s face and it was only then Crowley realized his hands had frozen in place as he stared. Michael, for his part, seemed well aware of the effect he was having on Crowley.

Crowley cleared his throat and looked back toward the mirror. “Yes. I trust you know the plan for the evening?”

“Business dinner at Gotham,” Michael replied. From the corner of his eye, Crowley saw Michael step forward, and then his hands were stilled by a touch of the younger man’s finger. “Not that tie.”

Crowley raised an eyebrow and looked at him. On top of being one of the most physically attractive men Crowley had ever seen, Michael Milton was extremely—dangerously, even—confident, if his commanding tone and presumptive touch were any indication. “Pardon me?”

Michael looked down at the half-finished knot, his long eyelashes hiding his eyes as he guided Crowley’s hands away and unwound the knot, pulling the tie down until the tail was loosed from Crowley’s collar. For whatever reason, Crowley was not inclined to stop him. “You’re meeting with Dick Roman. He’s a Type A, high-grade prick. He doesn’t do subtle.”

“It's a casual dinner,” Crowley said, but he had to admit he was intrigued.

“Yes,” Michael said, replacing the blue tie in the drawer and pulling out a dark burgundy one instead. “And I will bet you every penny of what you paid for my company tonight that he will show up in a professional three-piece power suit. Probably gray with a red tie. He’ll try to make you feel underdressed and, thereby, inferior.” Michael held the tie out to him. “Go with a full Windsor, the half just makes you look lazy.”

Without thinking about it, Crowley took the tie and eyed Michael, unsure of how to react to his calm confidence. Part of him found it extremely arousing, but he also didn’t care to be challenged by some boy who’d only just introduced himself. “I’ll take that bet.”

“Think I might keep you around if you’re that willing to throw your money away,” Michael muttered as he walked away and leaned back against the wall by the door, with a self-satisfied smirk.

* * *

“Bollocks,” Crowley muttered when Dick Roman and his wife were led through the restaurant by the host nearly twenty minutes late. He was, of course, wearing a slate gray three-piece suit with a shiny red tie done in a half-Windsor. “Are you interested in a career change, Michael? You’ve already proven yourself more useful than my assistant.”

Michael laughed and Crowley found it rather captivating. It was deep, husky laughter, and Michael threw his head back, exposing the long line of his throat, and his broad shoulders shook with it. “No, thank you, Mr. Macleod. I very much enjoy my job and have no interest in doing anything else for a living.”

He and Michael stood as the Romans approached the table, and Michael turned on all his charm. He smiled and made eye contact with Dick, shaking his hand firmly, and he flattered Mrs. Roman, complimenting her with a flirtatious smirk and kissing her hand before they all sat back down. The dinner went well, and as much as Crowley hated to admit it, Michael had been right about the tie. Dick had expected to be the more formal of the two, and when he wasn’t it put him off-balance and gave Crowley the upper hand.

Michael shrugged it off when Crowley mentioned it in the taxi on the way back to his condo. “In my line of work, it pays to be able to read people. I’ve been able to do it since I was a kid.”

“Well, you usually have to meet a man before you can get a read on him,” Crowley said. That had definitely been more than just reading people. “Do you know Dick Roman?”

“Other than what I’ve seen on TV?” Michael shook his head and smiled, a little bitterness creeping into his voice. “No. But I’ve known men like him, and they’re all the same.” He glanced over at Crowley and whatever he’d felt in that moment faded. “So, you have me for a couple more hours. Did you have anything else in mind?”

Crowley smirked and raised his eyebrows. “Given your… skills, I’m sure you could tell me what I have in mind.” His heart skipped a beat at the suddenly very predatory way Michael was looking at him. Crowley had just gotten himself into trouble, he was quite certain. 

Michael leaned across the car, one hand on Crowley’s thigh, squeezing lightly and moving slowly up. His breath was hot on Crowley’s neck, and his lips brushed against Crowley’s earlobe when he spoke again. “I could tell you.” Michael’s voice was low, but not quite a whisper, and it sent an involuntary shiver down Crowley’s spine. “But what would be the fun in that?” He lingered a moment longer and then moved back to his side of the car.

Unable to think of a witty response—really, Michael’s ability to leave him speechless was uncanny—Crowley licked his lips and openly stared. He was generally used to having all the power in a room, but Michael had been in control from the moment he’d stepped into the condo earlier that evening. It was an interesting—though not unwelcome, judging from his cock’s response—development.

The taxi pulled up in front of Crowley’s building and they both stepped out. Michael followed him past the doorman and into the elevator and kept his hands entirely to himself the whole way up to the twentieth floor and down the corridor that led to Crowley’s door. He could feel Michael’s eyes on him as he turned the key and walked in. 

Michael slipped his shoes off, pulling them neatly together and setting them on the rack by the door. “Tell me, Mr. Macleod,” he said, slowly, deliberately undoing the three buttons at the front of his jacket. “Do you know how to spot a submissive in a room full of people?”

Crowley was nervous as he watched Michael roll his shoulders to shrug off the jacket and hang it on the coat rack. It wasn’t the question that got under his skin, not really. The idea behind the question? That certainly had his attention. He also found himself wondering if Michael actually found him attractive. The man was probably seven or eight years younger than him, and even through the layers of clothes Crowley could tell he was well toned—probably frequently in the gym. Crowley wasn’t horribly out of shape, but he knew his body would be decidedly softer than Michael’s.

Michael took a step toward him, casually putting his hands in his pockets and wearing that very same knowing smirk he’d had when Crowley first saw him. He fought the instinctive urge to take a step back and cursed himself for somehow, unknowingly, ceding control of the situation. But his heart raced with the already building anticipation as Michael crossed the room toward him until they were only inches apart.

“All you have to do is pay attention,” Michael said, lifting Crowley’s chin with a gentle finger. “It’s plain to see in the way their eyes go wide when you’re in their personal space.” Michael guided them slowly to the bedroom as he spoke. “The way their breath catches in their throats when you touch them.” Crowley was caught up in the intensity of Michael’s blue eyes on his as he loosened the tie around Crowley’s neck. “The way they change their tie at your request without really knowing why.”

Crowley flushed a little then. He hadn’t thought about it at the time, but Michael wasn’t wrong. All of those things had happened when Michael had told him to change his tie. All of those things were happening right that moment with Michael towering over him—his presence more than his body, even though he was a few inches taller than Crowley—and Crowley’s cock was rock hard and straining against his pants already.

“Have you ever done this before?” Michael asked softly, deft fingers unbuttoning Crowley’s jacket and shirt before running flat palms up his chest and over his shoulders to push them off. Crowley just shook his head. “Mr. Macleod, this is very important and I need you to use your words. Can you do that for me?” Michael cupped his face in one hand, lightly brushing a thumb across his cheek and Crowley couldn’t remember the last time someone had touched him so tenderly.

“I have never been on this side of things before, no,” Crowley replied. He reached over and rested his hands on Michael’s hips, pleased when the touch wasn’t rebuffed.

Michael’s hand wasn’t holding Crowley’s face anymore, instead, his fingers traced aimless circles against Crowley’s back. “Would you like to? It doesn’t have to be anything crazy. We don’t have to do this at all if you don’t want to.”

Crowley’s hands were restless against Michael, running up and down his sides and feeling his body heat seep through the soft fabric of the dress shirt he still wore. “I’d like to, but I would rather not be restrained.”

“Of course,” Michael said. “We’ll go slow, no restraints, and you will tell me if it’s too much.” Crowley nodded. “I’m going to kiss you now, Mr. Macleod. Is that alright?” His eyes flicked to Crowley’s lips.

As if he would say no to that. “Please do.” His fingers tightened against Michael’s ribs as their lips met. The hands at Crowley’s back pulled him so that he was pressed against Michael’s chest, and he wrapped his arms around Michael’s waist. Crowley’s fingers explored Michael’s back, mirroring the slow determination with which Michael’s tongue explored Crowley’s mouth.

Crowley groaned as Michael gently rocked his hips and the full, hard length of his cock was trapped between them, the feel of it making Crowley’s twitch in response. His head spun and he was more than a little breathless when Michael broke the kiss, trailing his lips and tongue across Crowley’s jaw to suck an earlobe into his mouth.

Michael pushed Crowley back gently so he was sitting on the bed, and then he quickly unbuttoned his shirt and took it off, tossing it unceremoniously to the floor. Kneeling in front of Crowley, Michael reached for Crowley’s belt buckle and raised an eyebrow as though asking permission. Crowley nodded and leaned back, propping himself up on his elbows as he watched Michael unbuckle the belt, then unbutton his pants through hooded eyes.

Michael’s face was flushed with heat and Crowley couldn’t decide whether to watch the heavy rise and fall of his chest, or the way the muscles of his shoulder flexed, or his hands as they tugged Crowley’s pants down. He lifted himself off the bed a little to free them, almost as an afterthought. As Michael’s fingers traced a path back up the outside of his legs and hips until he reached the waistband of his boxers, Crowley kept his ass lifted off the bed so those could be pulled off as well. 

When Crowley’s long, thick cock was freed, Michael stopped for a moment and met his gaze with a raised eyebrow. Of everything he’d experienced over the course of the evening, that was the one thing he was used to. He chuckled at the surprise evident in Michael’s face. “Ten and a quarter inches,” he quipped, “if you’re looking for exact measurements.”

Michael bit his lip and looked like he was having some internal debate as he pulled the boxers down to pool at Crowley’s ankles and then pulled off his shoes and socks, moving Crowley’s legs so the pants were on the floor. He stood and shed his own pants, letting his length bob in front of him before taking it in his hand and lazily stroking a couple of times. Michael was nearly as big Crowley, but not quite as thick, and Crowley was utterly mesmerized by the way he touched himself.

Grinning wolfishly, Michael knelt over Crowley, straddling him. “Strip club rules, Mr. Macleod,” he said, catching Crowley’s reaching hand with his and placing it back on the bed. “I can touch. You may not. Is that something you can handle?”

Crowley’s voice was deeper, raspier than he was used to hearing it. “Yes, I can handle that.” He let his head fall back and moaned, fisting his hands in the bedspread as Michael rolled his hips and their trapped cocks rubbed together. 

Michael took his time exploring Crowley’s body with his hands and his mouth—his fingers combing through the curls of hair on Crowley’s chest, tongue dipping into the hollows above Crowley’s clavicles, teeth grazing the skin of Crowley’s shoulder—and tingling pleasure danced across his skin. “Swing your legs up onto the bed,” Michael said softly and he pushed Crowley’s shoulders until his back was against the mattress and Michael hovered over him. “Do you have condoms and lube nearby, or do I need to get them from my pants?”

“In the stand,” Crowley replied, his voice breaking in a way it hadn’t since he was a teenager. He was sweating and he moaned shamelessly as Michael rutted against him, biting his lip again with a breathless moan as their cocks glided against each other. “May I touch you now, Michael?”

Michael’s hand rested on Crowley’s chest and he shook his head. “Not yet. Okay?” Crowley nodded, and Michael reached for the bedside table, pulling open the drawer and rifling through its contents until he found what he was looking for and returned with a condom and a small bottle of lube that he set on the bed next to them. “Soon,” he promised, tenderly caressing Crowley’s face. “First I want to taste you.”

“Can you even fit my cock in that pretty mouth of yours?” Crowley had meant it to be snarky, maybe a little condescending, but the breathy rasp of his voice sounded more desperate to his ears than anything else. 

Michael laughed and raised an eyebrow over his dark, lust-filled eyes. “You’ve been doing so well for me, Mr. Macleod. Don’t ruin it by talking back now.” 

“Sorry,” Crowley responded lamely and then Michael was kissing and biting his way down Crowley’s chest and stomach, making his muscles twitch and drawing breathless sounds from him—sounds he hadn’t been aware he could make. He couldn’t remember ever wanting to feel someone’s skin beneath his palms, or hair between his fingers, as he did in that moment.

“Eyes on me,” Michael said, locking their gazes as he licked a stripe from Crowley’s balls all the way up his length, flicking his tongue at the tip. 

Crowley nearly swallowed his own tongue and his hips jerked involuntarily as he watched the entire throbbing length of his cock disappear into the wet heat of Michael’s mouth. Even at this angle, he could see the way Michael’s throat expanded to take him all the way in. Michael moaned around him, and it vibrated through him as he wondered how Michael could possibly be breathing. “Oh, god…”

Michael pulled back and held Crowley’s hips down as he sank down on his cock achingly slowly, over and over again until Crowley forgot how to think or breathe or exist beyond the sensation. He barely noticed when Michael reached for the bottle of lube and raised his knees to expose his hole. When a slick finger breached the tight ring of muscle Crowley cried out, and between that and Michael’s mouth, he was a moaning mess by the time a second finger was added.

Crowley let his eyes close and his head fall back against the bedspread as Michael released his cock with a lascivious pop. “Please,” he pleaded—and somewhere in the back of his mind, he protested that he absolutely did  _ not _ beg. “Michael, let me touch you.”

Michael pulled his fingers out, and Crowley felt his weight shift on the bed before the sound of foil tearing reached his ears. Moments later, Michael was leaning over him again, the head of his cock pressing blissfully past Crowley’s rim as he slowly buried himself to the hilt with a strangled moan. “Yes, touch me.”

Crowley didn’t have to be told twice; he pulled Michael down into a heated kiss, running his hands over any skin within reach and feeling the muscles in Michael’s back bunching and releasing as he thrust into Crowley. He wrapped his legs around Michael’s hips, heels digging into flesh, holding him tighter as his restless fingers traced across Michael’s skin of their own volition. 

The whole thing was far more intimate than anything Crowley was used to. They stared into each other’s eyes, whispered praise and pleas, and moaned and sighed their pleasure. He couldn't have closed his eyes or looked away if he wanted to, pinned by the intensity of Michael's gaze. How was it that one man, that he barely knew, could make Crowley feel like he was the only person on Earth at that moment? Crowley wondered for a passing moment if this was what it felt like to  _ make love _ . 

But he didn’t have time to contemplate it because Michael started stroking him in time with his quickening thrusts.

Michael must have felt the pulse in his cock because he buried his face in Crowley’s neck and growled, “Come for me,” against his skin. And Crowley did, crying out and squeezing Michael’s biceps as hot, sticky spurts covered his chest and stomach. Michael worked him through the orgasm, thrusting erratically for a few more seconds before he bit into the flesh of Crowley’s shoulder and stilled, a broken moan vibrating against Crowley’s skin.

Michael rested his forehead against Crowley’s, breathing heavily for a moment and pressing a chaste kiss to his lips. He pulled out with a low groan and sat back on his heels to take off the filled condom. “Trash?” he asked between panting breaths.

“Bathroom.” Crowley was still panting himself, still just across the line of too euphoric to move. He closed his eyes and listened to the sound of his own blood rushing through his ears, and of Michael shuffling around the bathroom. A moment later, he felt something warm and wet on his chest. Opening his eyes, Crowley saw him wiping up the mess of cum on his stomach, taking extra care to make sure he got it all out of the hair there.

“I’ll be right back, I’m going to get us some water,” Michael said. He was still gloriously naked as Crowley watched him walk out of the room, giving him a pleasant view of his ass. 

Crowley sat up and took the bottle of water from Michael when he returned. They both sipped quietly for a few minutes and then Michael turned to Crowley with a smile.

“You okay, Mr. Macleod?” he asked.

Crowley laughed and nodded. “It was certainly an interesting experience. No one’s ever had me begging to touch them before.” No one had ever taken the time to take care of him like that, he refrained from adding that particular part. Certainly, no one had ever bothered to ask how he felt afterward before. But he kept that to himself, as well.

“Unfortunately, our time is up for the night,” Michael said, glancing at the watch on his wrist, and he did actually sound as though he might be sad to leave. But he stood and searched out his clothes, pulling on his pants and shirt. “You should eat a snack before you sleep. And make sure you finish that bottle of water. You’ll do that for me, right?”

“Yes, of course,” Crowley replied automatically, cursing himself. Somewhere between tender touches and soul-piercing stares, he'd managed to forget that he had  _ paid _ for Michael to be there. How was he to have known it would be like this?

“Thank you.” Michael bent down and kissed Crowley one last time before he turned and headed for the door. “You know how to reach me if you require my company again, Mr. Macleod.”

And then he was gone, and Crowley was left alone with his confusion, contemplating how long he would have to wait to see Michael again.


	3. Chapter 3

**Summary for the Chapter:**

> Michael does have a life outside of work. Cas brings Michael a present.

**Notes for the Chapter:**

> Man, I almost didn’t think I was going to get this chapter done in time lol, it’s longer than the first two because for some reason this smutfest decided that actual plot is a thing that happens. Who knew? Anyhow, I hope you guys enjoy my first attempt ever at writing a threesome :D
> 
> Thanks to [Cutelittlekitty](https://archiveofourown.org/users/cutelittlekitty/pseuds/cutelittlekitty) for beta reading this for me!!
> 
> Chapter tags: Michael/Cas, Michael/Jimmy, Cas/Jimmy, Michael/Cas/Jimmy, Dom/sub dynamics, dom!cas, switch!michael, sub!jimmy, bottom!jimmy, threesome, blowjob, chastity, objectification, light bondage, anal fingering, anal sex, facial, coming untouched
> 
> Chapter 3 fulfills the CasJimmy square on my spn kink bingo card

Michael stretched, his back arching away from the desk chair, and ran a hand through his already disheveled hair. Not for the first time, he thought maybe he should hire someone to do this part of the job. But then, he supposed, his accounting degree—and all the money he spent on it—would be wasted. Besides, Michael liked having control over the back end part of the business, and it really didn’t take much of his time. He had hired a remote answering service to deal with calls, and the company website was automated, so all he really did when he sat in his rather expansive home office was push paper and crunch numbers.

Michael’s fees were paid into the Milton Agency’s corporate account because he didn’t want to do things differently than the ten other escorts he employed just because he was also the owner. Everyone received a weekly paycheck, including Michael, though his also included a meager salary for the accounting work. Escorts got sixty percent of the fees they brought in and the other forty was used to ‘keep the lights on,’ so to speak. Overhead on a business like this was not cheap, but Michael was smart, and a very savvy businessman.

He didn’t particularly care for the accounting; it was boring. Numbers and money were, however, some of Michael’s many talents, and he was usually only in his office for ten or so hours a week. Between that and the average of three nights per week spent with clients, he not only made more money but had more free time than any poor sap that was stuck in the vicious cycle of the regular nine to five grind.

On top of that, everyone he employed seemed to be just as happy with the Milton Agency as Michael was.

Michael spent another hour paying bills, cutting checks, and filing paperwork, and when it was all done, he was more than ready for an evening out. He tucked his cell phone and wallet into his back pockets, snatched the keys off his desk, and practically bolted out the door of his home office. His schedule said he was meeting Cas at The Rum House in just over an hour, and Michael knew traffic over the bridge would be a bitch at this time of day. He’d leave his car in the parking garage and hoof it to the closest subway station to hop on the F-train.

Taking the stairs two at a time, Michael made his way to the first floor of the penthouse apartment. He walked across the parlor and looked out one of the massive clock windows to take in his view of the East River and Lower Manhattan on the other side. He’d bought the place a year ago—a stroke of luck, really, that he’d been the first to put in an offer on the most sought after condo in Brooklyn—and he was still certain he would never tire of being able to look out over the city in every direction, especially at night.

The sleek, modern Clocktower penthouse had cost Michael a fortune, but as far as he was concerned, it was worth every penny. It had three floors and windows everywhere, and his own minimalistic taste in decor only made the interior more beautiful. It was certainly a far cry from the small mid-western town he spent much of his childhood feeling out of place in. He tore his eyes from the view, glancing down at his watch before starting toward the door. The full-length mirror hanging in the entry hall was Michael’s last stop.

Checking himself in the mirror, Michael turned to one side and then the other, examining the dark, slim-cut jeans he wore with a wide, black leather belt. His white tennis shoes were immaculate, as was the white dress shirt that was still tucked in—thanks to the advent of shirt-stays—with its sleeves cuffed just below his elbows to show off his sinuous forearms. He’d left the top two buttons undone while he was working, and as tempted as Michael was to leave it that way, Michael knew how much Cas liked him in a tie. He fastened the buttons and opened the door of the coat closet next to the mirror, pulling a wide black and gray striped tie off the back of it. He knotted it quickly and tucked it into his waistcoat—gray with black trim at the pockets. His hair didn’t have it’s usual artfully styled ‘just rolled out of bed’ look. Instead, Michael ran his fingers through a mass of natural curls, one of them falling over his forehead.

He looked  _ good _ .

Michael smirked at his reflection and then walked out the door, taking the elevator down to the first floor. 

“Afternoon, Mr, Milton,” the doorman said with a polite smile.

“Afternoon, John. How are Nancy and the girls?” Michael asked, clapping the older man on the shoulder as he held the door open.

“They’re great. Emily just won the lead role in the school play.” John’s eyes twinkled as he spoke, and Michael wondered for a split second what it would be like to have had a father that was ever that proud of his children.

Brushing it off, Michael smiled and stepped out of the building. “She’s going to be amazing. You have a good night, John. I’ll see you tomorrow.”

“Yes, sir. Thanks, Mr. Milton.”

Michael whistled a song he couldn’t quite put a name to as he walked down the sidewalk. The sun hung low, traveling slowly toward the horizon as the late afternoon heat simmered in the air around him. He made his way down the stairs and onto the busy platform of the subway station, only having to wait a few moments for the next train into Manhattan.

Halfway through the ride, his phone dinged and he pulled it out of his pocket to see an automated email had come through from the Agency’s website. Fergus—please, call him Crowley—Macleod had requested two hours of Michael’s time the following day for a client appreciation dinner. Michael normally didn’t work on Sundays, but it was only a couple of hours and he was willing to make an exception in this case. He enjoyed Mr. Macleod’s wit and charm, and the sex was hot. Sending a quick reply to the email, Michael let Mr. Macleod know he would be there and then shoved his phone back into his pocket, staring out the window until he reached his stop in Midtown.

The Rum House was a swanky bar with low lights and leather upholstery. The tables were never sticky and there was usually some local band playing. More importantly, Dean Winchester was the bartender, at least on Friday and Saturday nights. As he made his way across the floor, Michael could see Dean flashing his thousand-watt smile and flirting with a petite blonde as he mixed her drink.

“Well, ain’t you somethin’ fancy?” Dean asked, already pouring Michael a drink as he slid onto a barstool.

Michael laughed and took the tumbler of Booker’s. “What, this?” He grinned and gestured toward his clothes. “When you have a face this pretty, you gotta have the threads to match.”

Dean rolled his eyes. “Whatever, dude. You could be a fucking bum and you’d still be sexy as hell.” Dean and Michael had been friends since he first moved to New York, and while both of them had certainly done some growing up, some things never changed. Dean would always be a relentless flirt. It was in his DNA. “Meeting a client?”

“Yeah, he should be here any minute.” Michael sipped his bourbon and pretended he didn’t know Dean was really asking if he was there just to see him. It had been too long since he spent any time with his best friend. “What about you? How are Lisa and Ben?”

Dean shook his head, smile fading a little. “If I knew, I’d tell you. Lisa broke things off a couple of weeks ago.” Unsurprisingly, he did not elaborate. Dean wasn’t much for talking about his feelings. He was more the type to pretend he was immune to emotions and stuff everything down until he had an explosive meltdown. Of course, Michael was pretty sure Dean would feel better after his shift when he called the pretty blonde that was writing her number on a cocktail napkin as they spoke. At least temporarily.

Cas walked in then, his brother Jimmy trailing just behind him. They were identical twins, but the idea that anyone wouldn’t be able to tell the difference between them seemed ridiculous to Michael. They were like day and night. Cas’s hair was messy and untamed, his eyes dark and serious, and his posture impeccable—even with the visible tightness in his shoulders. Jimmy, on the other hand, had his hair neatly combed over and gelled to keep it in place, his eyes were bright and smiling, and he slouched a little—looking far more comfortable in the bar than his brother did.

“Listen, Dean,” Michael said, glancing back across the bar at his friend. “Give me a call, we’ll get shit-faced and you can tell me about what happened.” Dean smiled and nodded.

“That your guy?” he asked, gesturing toward Cas.

“Yeah,” Michael confirmed with a smile. “That’s my client and his twin brother.”

“You got a double dose of hot tonight, then,” Dean said. “I’ll leave you to it and call you later.” He walked down toward another customer at the bar, picking up the cocktail napkin with the cute girl’s number on it and stuffing it into his pocket on the way.

Michael spun in the barstool, waiting as Cas and Jimmy approached. “Hello, Castiel,” he greeted and then glanced over at Jimmy. “Have you brought me a present?”

Cas wasn’t big on public displays of affection, and anyone who didn’t know better might have mistaken the way he guided Jimmy forward by the elbow or the occasional incidental touches as nothing more than brotherly affection. Michael, of course, knew there was much more to it than that. He wasn’t one to judge, and if he were honest, he had no idea what their relationship was like when he wasn’t there. It was entirely possible that Cas just brought Jimmy around for Michael, but Michael sincerely doubted it. Not that he would ever ask. Anything that happened between them on their personal time was none of Michael’s business. Besides, he couldn’t deny that if he had the opportunity to fuck someone that looked just like him, he’d be all over it.

“Do you think you deserve a present, Michael?” Cas asked with a raised brow that made Michael’s mouth go immediately dry.

“Yes, Mr. Novak,” Michael replied confidently. “I believe I do.”

Cas smiled, guiding Jimmy to the stool next to Michael’s. He was so close that their thighs were nearly touching, and Michael could feel the heat of Jimmy’s body through his jeans. “I think so, too. Let’s have a drink and then we’ll take my car.” He waved Dean over and ordered a whiskey for himself and a cocktail for Jimmy.

“It’s been a while, Jimmy. How have you been?” Michael rested a hand on Jimmy’s thigh and squeezed lightly as he spoke. The question was sincere, of course. Jimmy was pleasant enough company, and Michael did like him.

Jimmy smiled easily and took a sip of his drink. “I’ve been well. I managed to lower the company’s tax bill by compensating employees with stock options.” His eyes flicked over to Cas and then back to Michael. “Castiel was pleased.”

Michael nodded knowingly as Jimmy’s hand snaked up his thigh. “Here I thought you were a present for me, but it sounds like I am a gift for you.”

“Don’t see why it can’t work both ways,” Jimmy replied with an impish grin, palming Michael through his jeans. 

Castiel raised an eyebrow as Michael met his eyes. “Finish your drink,” he ordered, reaching over to take Jimmy by the wrist and pull his hand away. “You may touch when I say and not before.”

Jimmy nodded, resting the offending limb on the bar when Cas released him. “Yes, Castiel.” He didn’t rush through his drink. In fact, Michael was quite certain Jimmy was drawing the tension out intentionally, possibly trying to make Cas regret making him wait. Jimmy could be quite the brat when he wanted to be. Cas seemed unperturbed by his insolent display. 

Michael, on the other hand, was getting very impatient for what promised to be a fun night. He glanced up at Cas. “Am I allowed to touch?”

A slow, dark smirk pulled at the corner of Cas’s lips, and the smoldering stare sent sparks of arousal through Michael’s body, straight to his already swelling cock. If Cas had asked, Michael would have bent Jimmy over the bar and fucked him until he was a sloppy, screaming mess right there in that room full of people. “You may. He is a gift for you, after all. No matter what he might say.”

Michael grabbed Jimmy by the chin, turning his head so their eyes met. Jimmy’s eyes were already wide and lusty, a little spaced out, and Michael pulled him in slowly, sucking a plush lower lip into his mouth. Despite the fact that they had the same face, kissing Jimmy was nothing at all like kissing Castiel. He was soft and pliant, allowing Michael to  _ take _ and be as demanding as he wanted to be. Michael’s fingers trailed down Jimmy’s throat, wrapping softly around the yielding flesh as he claimed every part of Jimmy’s mouth with his tongue and swallowed the already desperate, breathless sounds he made. When Michael broke away, Jimmy was panting.

“It’s time to leave, James,” Michael informed him in a low whisper. “Finish your drink.” 

Jimmy’s fingers trembled slightly as he wrapped them around the long, delicate stem of the martini glass that held what was left of his cocktail. He downed the rest of it in one swallow and set the glass gently on the surface of the bar before standing. “Okay. I’m ready now.”

Castiel dropped a bill on the bar with their empty glasses and led them out the front door of The Rum House. 

Michael’s nerves were already singing with anticipation when they reached Castiel’s car, and he was ushered into the back seat next to Jimmy. Castiel had barely pulled out onto the road, and Michael was already pulling Jimmy into his lap, grinding up against him and teasing his nipples through the white dress shirt he wore. He made sure they were in the middle of the back seat and met Cas’s eyes in the rearview mirror as tilted Jimmy’s head to one side to trail soft, wet kisses down the exposed skin of his neck.

Jimmy’s whiny, needy moans were nothing like the deep groans that vibrated from Castiel’s chest when he was buried inside Michael. It was an intoxicating experience, meeting Cas’s intense gaze in the mirror while gripping Jimmy’s hips to pull him down against the thick, hard length of his cock. Michael could almost— _ almost _ —pretend it was Cas in his lap. He let one hand trace Jimmy’s hipbone inward and down to his groin, and he cupped Jimmy’s dick and let out a surprised gasp.

“Is that what I think it is?” Michael asked, whispering softly into Jimmy’s ear as Castiel took a left turn at a traffic light. Jimmy just bit his lip and nodded. “How long have you had that pretty cock locked away?”

Jimmy whimpered softly as Michael pinched and pulled at one of his nipples, and his hands fisted against the leather of the back seat on either side of Michael. “Three weeks,” he answered.

Michael hummed against Jimmy’s shoulder. “And are you allowed to come tonight?” Jimmy’s gaze flicked up to the rearview mirror, but Cas wasn’t looking at them that moment. He looked away and didn’t answer. “If you don’t tell me, I’ll just ask Castiel. I don’t think he’d like it very much if I told him you refused to answer such a simple question.”

Jimmy shook his head. “Technically no, but Cas said I could earn it.” His eyes were full of an endearingly hopeful expression, and Michael smiled softly at him, and then he squeezed the inside of Jimmy’s thigh and latched on to suck a mark into the flesh at the crook of his neck.

Castiel was pulling the car into the darkness of a parking garage and pulling into a spot very near the elevators a moment later. Always the gentleman, he opened the door for Jimmy and then Michael to get out of the car. When the elevator doors slid smoothly, silently shut behind them, Michael found himself standing between the twins for the ride up.

Jimmy was quiet, standing with his hands clasped behind his back, but there was an undercurrent of excitement in the way he shifted from one foot to the other and the way his fingers tapped against the back of his hand. As soon the elevator started moving, Castiel bodily pinned Michael against the back wall, but he didn’t otherwise touch him, just stared down at him with those intense, stormy blue eyes for a moment before speaking, his low voice.

“Are you enjoying the toy I brought you?” he asked, fingers trailing roughly down Michael’s neck before gripping his tie just below the knot.

Michael nodded. “Yes, Mr. Novak.” 

Castiel’s gaze softened only slightly. “I’m just Castiel tonight, Michael. As long as you remember that Jimmy is just a plaything for you tonight.” He tugged on the tie, bringing Michael’s face closer to his. “And every little sound you make, every word you say, belongs to me. Are we clear?”

“As crystal, Castiel,” Michael answered, involuntarily licking his lips and trying not to close the centimeters of distance between their mouths. As much as he might enjoy Jimmy’s company, Michael couldn’t imagine him ever being anything more than a shared toy. There was no universe in which Jimmy could ever possibly hold a candle to Castiel. 

“Always such a good boy for me, Michael.” Castiel gently patted Michael’s cheek with one hand, then stepped back with a dark smirk.

Michael was disappointed that Cas hadn’t kissed him, but he pushed it aside and took the moment to remember how to breathe before the doors opened into Jimmy’s Manhattan penthouse condo.

Castiel was the first out of the elevator, wordlessly leading them through Jimmy’s apartment and into the bedroom. The room was large and open with very little in the way of decor, and an entire wall of floor to ceiling windows overlooking the lights of Manhattan. In the center was a huge four-post bed, the California King mattress covered with several pillows and a pale blue comforter. Castiel was already taking off his jacket and his tie when he turned to face Michael and Jimmy.

“Jimmy,” he instructed, “be a doll and undress Michael for me.”

Jimmy walked around until he was standing in front of Michael, and his fingers trembled just slightly as he reached for the buttons of Michael’s vest. As he undid them one by one, Michael kept his eyes on Cas. Jimmy’s hands glided up Michael’s chest, pushing the vest over his shoulders, as Cas’s sure fingers deftly unbuttoned his own shirt. As Michael’s tie was loosened and pulled free, Cas’s belt was unbuckled and slid from the loops. It continued that way until Michael was standing naked in front of Jimmy, and Cas wore only his black slacks.

Michael’s heart beat erratically against his ribs as he watched Cas slowly rake his gaze down every inch of his body, resting momentarily on the twitching length of his erection. He was standing at the side of the bed, and he beckoned Michael to him. Cas’s arm snaked around his waist when he approached, and he pulled Michael against him, grabbing a fistful of hair and tugging it to tilt Michael’s head back. Michael’s hands were on Cas’s shoulders, and his breath shook as Cas trailed soft, full, gentle lips over his throat. Then, without warning, Cas spun him so he was facing Jimmy again.

“Go ahead, Michael,” Cas said, tracing the lines of muscle on Michael’s torso as he spoke. “Tell him what you want him to do next.”

Thinking was certainly not Michael’s strong suit when Cas was wrapped around him like this, in an almost loving embrace as he stroked fingers softly against Michael’s skin. But being obedient was something he was always good at. “Take off your clothes,” he ordered Jimmy, only the slightest tremor in his voice as Cas’s hand closed loosely around his cock and teased at jerking him off.

As Jimmy unbuttoned his shirt, shrugged it off his shoulders, and let it fall to the floor, Michael let himself imagine that it was Cas stripping for him, pulling the white undershirt up over his head to expose gloriously flat, toned abs and muscular chest. Then sliding down his pants to reveal thick runner’s thighs and white cotton boxers. Michael’s hands fisted into the fabric of Cas’s slacks as Jimmy pulled the waistband of his boxers down over his sharp hipbones, letting them slip down and pool at his ankles so he stood entirely naked and too far away for Michael to reach out and touch him.

The momentary illusion Michael had indulged in was broken by the sight of the bright, baby blue cock cage nestled against the dark curls at Jimmy’s groin. But  _ fuck _ , Jimmy standing there, looking at Michael with slightly parted lips and wide blue eyes was still a beautiful sight, and Castiel was gracing Michael’s shoulders with hot, wet kisses and stroking his cock painfully slowly. On those occasions that Michael’s services were requested by a couple, it was exceedingly rare that he was the center of attention, and he basked in it when he was.

Castiel’s voice was a rumble emanating from his chest and vibrating against Michael’s skin when he spoke. “Come over here and kneel,” he commanded, and Michael nearly dropped to his knees himself before he remembered that Cas was talking to Jimmy.

Michael felt like he’d barely had time to blink before Jimmy was kneeling before him, looking up with a crooked, expectant smile. His tongue darted out, wetting his lips. “May I suck your cock, Michael?” he asked, his voice soft, almost shy.

“Open your mouth,” Michael groaned in response, letting Cas guide his erection forward until the head was resting on the full softness of Jimmy’s lower lip. Then Cas pressed his hips and the full length of his hardness against Michael’s ass and he was enveloped in the wet heat of Jimmy’s mouth. 

_ Holy shit _ , Jimmy was good at this. Michael moaned and let his head fall back against Cas’s shoulder as Jimmy took as much of his cock into his mouth as he could, the flat of his tongue pressing against the underside of it on the way down and circling the head on the way up. Jimmy made blissful little noises that sent jolts of pleasure through Michael.

Castiel toyed with Michael’s nipples—pinching, pulling, twisting just slightly—and then as if he could read Michael’s mind, one hand slipped down the twitching muscles of his abdomen and reached over to thread fingers into Jimmy’s hair as Michael looked down at him. Jimmy turned his gaze up to meet Michael’s, and Cas was guiding him, making him take Michael’s entire length into his throat until his nose was pressed into dark curls, and Michael’s knees went weak.

“Fuck, Jimmy,” Michael breathed, and suddenly Castiel was pulling Jimmy off of Michael. Jimmy whined and Michael’s cock twitched. 

“Who does your pleasure come from, Michael?” Cas’s voice was a dark, low whisper that sent shivers down Michael’s spine.

He’d forgotten himself already. “You, Castiel. I’m sorry.”

Castiel’s gentle fingers turned Michael’s head so their eyes met. “Shh. I’m not going to punish you too harshly this time. Don’t forget again.” Castiel released him and walked over to the bed, leaving Michael to stumble slightly at the loss of support. He was still facing away from Michael when he took off his pants and boxers in one smooth motion, bending over and giving Michael an exquisite view of his perfect ass. Then he climbed onto the bed, nestling into the pillows on his knees and ordered Michael and Jimmy to join him. “Lie on your back with your head between my knees, and put your arms over your head.”

Michael did as he was told, doing his best to ignore the fact that Cas’s cock was rock hard and hanging just above his face as he rested his arms on either side of Castiel’s knees. Cas reached behind him and pulled up a leather cuff that was connected to an elastic band that disappeared somewhere Michael couldn’t see from his angle.

“I’m going to cuff your wrists. You should be able to move enough to stay comfortable,” Cas explained. “Is that okay?”

Michael eyed the cuff for a moment and then nodded. “Yes, Castiel.” Then leather straps were around his wrists and he tugged at them gently to test his range of motion before letting his arms rest against the pillows. 

Castiel was leaning over Michael then, directing Jimmy until he was positioned straddling Michael with his caged cock hanging over Michael’s face and his mouth close enough to Michael’s dick that his hot breath fanned over it enticingly. He looked down at Michael and smirked. “I’m going to open Jimmy up for you, and you’re going to watch. Nothing else.”

Michael whimpered just a little because every time his cock twitched, it brushed against Jimmy’s lips and the temptation to lick the bead of pre-cum off the tip of Cas’s dick was almost too much. It was  _ right there _ and he wouldn’t even have to move his head. But he bit his lip and stayed still.

He heard the distinctive pop of the cap of a bottle and then Michael’s eyes were caught by the fingertip he could just barely see at this angle was slowly circling Jimmy’s rim and then disappearing past the tight ring of muscle. 

Jimmy’s breathing hitched and he moaned, rocking slowly back onto Cas’s finger until a second was added. Michael was having a difficult time focusing; there were so many things going on at once, so many things he wanted. He wanted Castiel to be adding a third finger to stretch him open, instead of Jimmy; he wanted to bury his aching cock in Jimmy’s tight ass; Michael wanted to blow Cas until he came so hard it dripped down his chin.

Instead, he whined and watched as Jimmy’s cock leaked through the slit in the cage when Castiel found his prostate. It dripped, hot and slick onto Michael’s face, mingling with the barest drops of precum that rolled off the tip of Cas’s dick, still hanging hot, heavy and  _ so fucking close _ to Michael’s lips that he could almost taste it. His own length was throbbing, a little painful at the lack of attention, and Michael pulled at his restraints. It was damn near involuntary to try and reach for it, to ease the ache just a little. The only things he managed to lay his hands on were Cas’s thighs.

Jimmy keened and rode Castiel’s fingers, and Michael groaned. It was an overwhelmingly pleasurable frustration. “Cas, please,” Michael breathed and his fingers dug into the meat of Cas’s thighs. “Please let me do something.” 

Castiel’s smug grin was incredibly satisfying. “What would you like to do, Michael?”

A thousand different things crossed his mind, but Michael settled on, “I think my toy is ready. I want to fuck him.”

“Jimmy,” Castiel said, ignoring the whine from his twin as he pulled his fingers out. “I want you to ride Michael’s cock until you’re both begging me to let you come.”

Jimmy didn’t waste any time, turning so he faced Castiel and lining himself up with Michael’s length. He lowered himself slowly and Michael wasn’t sure which of them the deep, broken moan came from. Castiel was leaning back now, stroking himself firmly, but without urgency, and licking his lips as Jimmy rose up and slammed himself back down onto Michael’s cock.

Michael was nearly ready to beg for release right then and there, but the only sounds that escaped him were the groans as Jimmy rode him. He could hear it in Jimmy’s high, breathy whines that he was in the same boat, but Michael couldn’t take his eyes off of Cas. He watched Cas’s hand sliding up and down his thick shaft, thumbing the head every so often and bit his lip.

It was Jimmy that broke first, promising to come on Michael’s cock without taking off the cage. “Please, Castiel,” he whined, never slowing his pace. “Please let me come.”

The words pulsed through Michael, tightening in his groin until he thought he might literally explode. He didn’t even realize that his own rough voice had joined Jimmy’s in the plea for release until Castiel relented.

“Come for me,” he said, eyes flickering back and forth between Michael’s face and Jimmy’s and furiously pulling at his own cock. 

Michael came in hard pulses that left him blinking back white spots and gasping for air as he emptied himself into Jimmy, and he could feel Jimmy clenching around him, wet warmth coating Michael’s lower abs.

Castiel breathed erratically, and he threw his head back as his release hit him, spilling over his fingers and gushing onto Michael’s face as he worked himself through it. 

Michael licked his lips, reveling in the salt tang of Castiel on his skin, and closed his eyes. The three of them stayed there like that for what could have been forever. Michael had lost all capacity to judge the passage of time. He was sticky and sweaty, his body sated and languid, and he really wasn’t certain he would be able to move if he was asked to. He felt his softening cock slip out of Jimmy as the cuffs came off his wrists, and he opened his eyes to see Jimmy lying next to him on the bed, a similarly lazy smile on his face.

Castiel cleaned them all up, and then the three of them were a tangle of limbs, falling asleep without the energy for proper good nights.


	4. Chapter 4

**Summary for the Chapter:**

> Michael gives up a night off to attend a client appreciation dinner Crowley’s company is holding.

**Notes for the Chapter:**

> Herreeeeee a day late with a new chapter!!
> 
> I wanted to share a couple of things with you guys. Anyone who knows me, knows that when I use real cities, I like to use _real places_. So, every restaurant, bar, club, apartment, etc that I actually name or describe in this fic is real. That being said, I'd like you to see the virtual tour of Michael's $15mil condo in Brooklyn.
> 
> [The Clocktower Penthouse](https://youtu.be/3zkEU-FplCg)
> 
> Also, here's the song Michael's listening to in the tub [Piano Sonata No. 13](https://open.spotify.com/track/21WJfd3z1hielSG5wx6cdf?si=aHOn-sQJSBmlaehuKF4VLg)
> 
> Hope you guys like this chapter :D

Michael laid on his couch in nothing but a pair of soft black sweatpants with one leg up on the back, moving his foot in time with the music as he watched Fred Astaire twirl Ginger Rogers across his TV. He was still a little tired when he got home after leaving Jimmy’s apartment, so instead of going to the gym like he normally would have, he spent the day lazing around his condo. The only thing he had to do that day was meet Mr. Macleod at The River Café in an hour, but there was no real rush as it was just a few blocks away.

It wasn’t very often he saw a new client again so soon after their first meeting, and he definitely wasn’t typically one to sacrifice a day off, but something about Mr. Macleod made Michael want to see him again. And it was only a few hours at a fancy restaurant. No skin off his nose, if he was being honest. He smiled, wondering if Mr. Macleod would wear the blue tie as Michael had instructed him to in the email he sent agreeing to the date.

His cellphone vibrating across the coffee table roused him from his thoughts, and he reached over to pick it up. Lucifer. Of course. Michael swiped his thumb across the glass to answer. “Hello.”

“ _ Hey, everything okay? _ ” his brother asked on the other end of the line. “ _ You totally blew me off at the gym this morning _ .”

Michael sighed. “Yeah, Luke, everything’s fine. I was just a little tired and I forgot to call you.”

“ _ Long night? _ ” Lucifer snorted and Michael could almost hear the grin in his voice. Of the few family members he still kept in touch with, Luke was the only one that actually knew Michael was an escort. Not because he was ashamed of his job, just because he didn’t care to share his life with his family. Luke was different. They had always been close, ever since they were kids.

“Oh yeah. Totally worth the exhaustion.”

“ _ Alright. Don’t flake on me next time, asshat _ ,” Luke said. “ _ And make sure you’re taking care of yourself _ .”

Michael rolled his eyes, but he appreciated his brother’s concern. Saying his goodbyes, he ended the call and stood, stretching his arms languorously toward the ceiling with a yawn. He tossed his phone down onto the couch and ambled over to the stairs, taking them all the way up to his bedroom on the third floor. He stripped his sweatpants off and folded them neatly, setting them at the foot of the king-size bed he would very much have liked to lie down on at that particular moment. Eying the dark blue comforter, he considered sending Mr. Macleod another email with apologies, saying that he wouldn’t be able to make it after all.

But then Michael remembered the way the man’s eyes had gone wide, and the subtle part of his lips when Michael invaded his personal space and decided he definitely wanted to go to this dinner. But as he was working on his night off, he most definitely would not be wearing a tie. He’d already picked a suit anyway. He pulled on the gray slacks and a white dress shirt, buttoning all but the top two buttons and tucking it in. The blazer that matched the pants went on next, and he buttoned the top button. 

Walking over to the full-length mirror, Michael checked his reflection and adjusted the collar of his shirt so that the dip of soft flesh between his clavicles was clearly visible. His hair was a mess, sticking up in all directions—and not in the sexy way he normally wore it—so he grabbed a comb off his dresser and dragged it through his thick locks until they cooperated. It was a bit neater than his usual style, but it still looked good. Black socks and Italian leather shoes, his platinum Rolex, and a plain, thin silver chain went last, and then he went into the bathroom and brushed his teeth.

Twenty minutes later, and after a cup of strong coffee, Michael was walking down the sidewalk toward the river with his hands in his pockets. It was hot, but at least the cloud cover kept the sun from beating directly down on him. He was early, but Mr. Macleod was already waiting for him outside, looking rather dapper in a dark blue suit, crisp white dress shirt, and the blue brocade tie he’d wanted to wear to meet with Dick Roman.

Michael walked up to him, immediately reaching out to straighten the knot. “That’s a nice tie, Mr. Macleod,” he said with a smirk, very much enjoying the tinge of pink in his client’s cheeks. The man looked him over, eyes wandering slowly and eventually resting on the skin exposed by Michael’s undone top buttons. “Shall we go in?”

“Yes,” Mr. Macleod agreed. “But do us a favor and don’t call me Mr. Macleod.” 

“I think I can manage that.” They walked in, and Michael nodded politely at the host as they breezed past him. The restaurant was beautiful, with its shiny oak bar and tables. It was easy to spot their group. A few very well dressed people, undoubtedly other editors and publishers that Mr. Macleod worked with, surrounded by several men and women with slightly less expensive tastes. The clients to whom the company was showing its appreciation. Writers who, for the most part, looked as though they were far more comfortable in a quiet room with a laptop than a fancy restaurant that charged twelve bucks for well drinks.

“It should be a casual enough dinner,” Mr. Macleod said. “Raphael will probably make a speech, but other than that we’ll be left mostly to our own devices.” 

Michael did note that most of Mr. Macleod’s coworkers had not brought dates with them. It was a bit unusual, as most of the time when people requested his company at a party like this it was because they didn’t want to be the one that showed up alone. They sat down at the long table and ordered drinks, and Michael was introduced to several people whose names he filed away for use at this dinner and any other potential company events. Apparently, he hoped Mr. Macleod would become a regular.

Raphael did, in fact, make a speech before their dinner was brought out, but after that drinks flowed freely and conversation was lively. One particular author named Garth talked Michael’s ear off about his latest novel.

“All my books are about supernatural creatures,” he said, with a lively smile. “This one’s about angels and demons. Lots of intrigue. It’s gonna be great!”

The kid clearly loved writing, and Michael let him talk, nodding and smiling politely as he went on about how he tweaked the original mythology to suit his needs. Creative license and all that. Despite his religious upbringing, Michael was far more interested in pagan mythologies than those of modern religion. They were more interesting, the characters more relatable. Eventually, Garth lost interest in talking to Michael and moved on to some other poor victim.

Nearly an hour and a half passed before Michael and Mr. Macleod actually got the chance to speak to each other. Mr. Macleod looked a touch exasperated by the whole ordeal, and Michael reached over and squeezed his knee gently. Their eyes met and Mr. Macleod’s shoulders relaxed a little and he smiled.

“Are they all like that?” Michael asked, gesturing vaguely in Garth’s direction. The writer was animatedly going on about how each of the angels in his book had different color wings.

Mr. Macleod chuckled and shook his head. “There definitely isn’t anyone else like Garth. But generally speaking, writers fluctuate between acute self-loathing and wanting to burn everything they’ve ever written, and being extremely proud of the work they’ve done and wanting to share it with everyone they meet. It’s a cycle.” He leaned forward, resting his elbows against the table and lacing his fingers together. “So, what do you do when you’re not working?”

The question was asked with the practiced casualness of pointed small talk, made to sound like the conversation was simply meant to pass the time. Michael could read people well enough to see that Mr. Macleod asked the question because he was, in fact, interested in the answer. 

“I’m very boring outside of work,” Michael said, pausing to sip from his drink. “I go to the gym a few days a week. I read. I watch movies. I don’t have any terribly interesting hobbies.” As always, he was careful not to let too much of his personal life slip into the conversation. As long as he kept things vague, it was still just small talk. “What about you, Crowley? How do you like to spend your free time?”

“I’m an editor, I don’t have free time.” He downed the rest of his drink. “Bit of a workaholic, if I’m being honest. On the rare occasion that I am not falling asleep on my sofa with a manuscript, I enjoy movies.” Crowley paused, contemplative eyes on Michael’s face. “Perhaps we could dispense with the small talk and have a conversation like normal people.”

Michael hesitated. He liked Mr. Macleod, at least what he knew of him so far, but they weren’t ‘normal’ people, and this wasn’t a ‘normal’ relationship. It would be far too easy to cross the line between professional and personal and Michael did not allow himself to get emotionally involved with his clients. That never ended well. Apparently, his brain and his mouth were not on the same page, however. “Yeah, that would be nice,” he said softly. 

They were both silent for a moment after that, unsure of how to proceed. Michael wasn’t used to not knowing how to keep a conversation with a client going, but the truth was that he never really had meaningful talks with them. He preferred it that way. Now, he was struggling to find something that would walk the line between small talk and real talk, and it took him a minute and the rest of his drink to settle on something he knew they had in common. 

“What’s your favorite movie?” Michael asked, breaking the silence. He rested his elbow against the table and propped his chin up with a hand, giving Mr. Macleod his undivided attention.

Crowley smiled, setting his empty glass down against the table. “ _ Double Indemnity _ .”

Michael nodded, relaxing a little. He could talk about movies. They’d get to know something about each other, and it wasn’t so personal that it made him uncomfortable. “Good choice. I enjoy a good film noir.”

“I like good drama, generally. Film noir tends to have just the right amount of it. What about you?”

“ _ Gone With the Wind _ .” Michael flagged down a waitress and ordered another drink for himself and Crowley.

Crowley raised an eyebrow. “Really? That’s quite a surprise.”

“What? That I like romantic movies?” Michael asked with a grin, pretending he wasn’t wondering when he’d stopped thinking of the other man as Mr. Macleod and started thinking of him as Crowley. Similarly, he pretended he wasn’t staring at Crowley’s expressive face. It wasn’t as if Michael hadn’t found him attractive before, because he had. It was just that Crowley had an interesting face, with his sharp jawline and slightly pointed chin, deep-set brown eyes, and straight nose. Michael was definitely not staring at his client with any kind of personal interest whatsoever. 

“Well, yes, a bit.” The waitress returned with their drinks and Crowley took them with a polite thank you. He handed Michael his, and if Michael’s heart skipped when his fingers brushed against Crowley’s, he kept it to himself. “But in this case, I just thought you’d at least have better taste.  _ Casablanca  _ is a far better romance.”

Michael laughed, probably a little more loudly than was appropriate in the River Café, but he was on his fourth drink and feeling the buzz of intoxication, so he didn’t really care. “First of all,  _ Gone With the Wind _ is a damn good movie and an even better book.”

“Selznick fired George Cukor because he didn’t think a gay man could direct love scenes between a man and a woman.” Crowley was clearly offended by the idea, his eyebrows drawing together as he said it.

“It was the 30s,  _ Fergus _ ,” Michael said, smiling when Crowley glared at him. The man certainly had a well-practiced bitch face. Michael was just tipsy enough not to pretend he didn’t think the reaction was cute. “And besides, he still coached Vivien Leigh. They just didn’t tell Selznick.”

They continued to debate the pros and cons of Gone With the Wind as time passed and the other dinner attendees trickled out of the restaurant, each stopping to bid their farewells. By the time they reached the agreement that Scarlet was a stone-cold bitch who got exactly what she deserved, they were the only ones left. Michael wasn’t sure when the evening had started to feel like a date—a real date, not the kind he got paid for—but he glanced down at his watch and realized that Crowley’s time had run out just over an hour ago. Shit. It wasn’t at all like him to lose track of time like that.

“Well,” Michael said when Crowley was done talking. “I’ve been here for a bit too long. I should go.” He reluctantly rose from his chair, and Crowley did the same. “I won’t charge you for the extra hour; it’s my fault. I lost track of time.”

Crowley seemed a little disappointed, and Michael would be lying if he said he didn’t feel it himself. He was enjoying the evening, but even tipsy as he was, Michael knew if he stayed any longer he would be stepping further across the line between professional and personal than he was willing to. 

“I’ll walk you out,” Crowley said, putting his hands in his pockets with a small, forced smile. Michael just nodded and they made their way outside. The air had cooled considerably and the asphalt was wet, the red of the nearest stoplight reflecting in a small puddle. Michael turned to face Crowley, who took his hand and pressed a stack of bills into it. “For the extra time,” he said. “I won’t take no for an answer, so don’t bother.”

“Alright,” Michael agreed reluctantly, stuffing the money into his pocket. “Have a good night, then.”

“You, too,” Crowley replied.

Michael turned to leave and took a few steps in the direction of his condo before stopping in his tracks. He should have kept walking, he knew, but instead he turned back to see Crowley was leaning against the wall and watching him. He was definitely toeing the line as he closed the short distance between them and caught Crowley’s lips with his. The kiss was short, chaste, but surprisingly intense. Michael’s hand was on Crowley’s cheek when he pulled away and smiled. “I had a good time tonight, Crowley. Thank you.”

Without waiting for a response, Michael shoved his hands in his pockets and turned away. The walk home wasn’t much, but it was long enough to sober him up a little. Just enough for him to really consider the fact that the whole evening had felt much more intimate than Michael should have allowed as he walked through the front door of the building. He didn’t want to give Crowley— _ Mr. Macleod _ —the wrong impression. Especially not when it seemed so clear that he’d only hired Michael for the night because he wanted to spend time with him. With the short amount of time he’d booked, he had to have known that sex wouldn’t even be on the table.

Shit, Michael thought as he opened his door.

What did it matter why Crowley had hired him? And Michael may have lost track of time, and kissed him unexpectedly at the end of the night. But that was just because he’d had one too many drinks. Next time, he would just be sure to stay sober. If there was a next time, of course. He took the stairs two at a time up to the bathroom. Through the large windows, he could see that the clouds had mostly cleared out, revealing the few stars that could be seen in the sky over New York. It was a nice night for a bath. He could lie in the tub and clear his mind before he went to bed.

Michael let the water run until it was steaming, then put the stopper down, poured some lavender-scented bath foam, and let the tub fill as he stripped off his suit. He pulled his phone out of his pocket and thumbed through his music until he found a classical playlist and he let that play. Stepping into the tub, he turned off the water and submerged himself up to the neck with a content sigh. He laid his head back and looked up through the slanted skylight and tried to make his mind as blank as the black night sky above him.

Between Mozart’s Piano Sonata No. 13 and the light scent of lavender in the air, Michael started to drift, his eyes closing. His mind was blank, nothing but the soft notes of the piano reverberating, for a while. But it wandered eventually, and he found himself thinking of Crowley. Michael tried, without much success, to direct his thoughts away from Crowley’s crooked smile and throaty laugh, the way his eyebrow arched elegantly up every time Michael said something that put him on his heels, and the pink tinge the spread across his cheeks when Michael complimented him. He tried to ignore the warmth that spread through him from his chest when he thought about Crowley.

He couldn’t get emotionally involved with a client, not again. There was a reason he never let himself feel anything more for Cas, even though Michael knew under different circumstances they could be so much more than they were. But for some reason, even though he really barely knew the man, Michael could not stop thinking about Crowley. Maybe it was just an infatuation, something he needed to get out of his system. Once he’d done that, Michael could go back to business as usual.

Michael’s hand moved unbidden, slipping down the skin of his stomach, fingers sliding down the length of his cock, lazily teasing until he was hard. His imagination conveniently supplied him with the memory of Crowley’s unbroken eye contact as Michael sank into him, and the way his lips parted with a deep groan. Michael mirrored the sound as he stroked himself more firmly.

He imagined Crowley laid out against the dark blue spread on Michael’s bed, wrists tied to the headboard with that dark red tie. Michael bit down hard on his own lip, thumbing the head of his cock and hearing the rasp of his name roll off Crowley’s tongue as he begged to be fucked. Seeing the way Crowley looked up at him with just a little more than lust in his eyes when Michael finally gave him what he wanted.

Water sloshed over the edge of the tub and splashed against the tile as Michael’s hips jerked and a breathy moan escaped him. Heat built quickly in his pelvis, and he moved his hand faster over his shaft. Crowley would let out little, broken moans and pull against the tie to try and touch Michael.

“Crowley,” Michael groaned as his release hit, curling his toes and tightening his muscles. He came with such intensity that the first heavy spurt of it broke the surface of the water. It felt much cooler than it had when he stepped into it. 

Michael sloshed around in the water to clean himself off, then stepped out and reached for the towel hanging on the wall by the shower. He shouldn’t have done that; it definitely had not gotten Crowley off his mind. In fact, Michael was pretty sure he was only going to be thinking about Crowley more. He should probably remove Crowley from his list of clients and move on, but he knew he wouldn’t. Michael was already too attached. He shoved whatever his developing feelings might be into a little box and hid it in the recesses of his mind. 

Feelings were nothing but trouble.

“Fuck.”


	5. Chapter 5

**Summary for the Chapter:**

> Michael and Anna go to a wedding reception, but Michael isn’t feeling quite himself.

**Notes for the Chapter:**

> Holy hell, you guys! This chapter is late AF and I am so so sorry! I have been going through some major real-life stuff and things, to include some trouble with my mental health and a move out of state. Anyway, here’s the thing! I hope you like it :D
> 
> Written for @spnkinkbingo 2019.
> 
> Special thanks to @fangirlingtodeath513 for beta reading for me and an extra special thanks to her, @galaxystiel, @phoenyxnova, @cutelittlekittykorner, @malmuses, @imbiowaresbitch, and @winchester-ofthe-lord for being super supportive through the craziness that my life has been over the last couple of weeks. 
> 
> Chapter tags: blowjob, public sex, girls night, rom-coms, Michael talks about his feelings, Anna is a good friend, wedding reception, drinking, wine, ice cream and movies, FEELS

The party was lively, the generous open bar lubricating social gears so even the wallflowers mingled. It was a massive event with some of New York’s most prominent people in attendance. There were more than a few familiar faces in the crowd; most Michael recognized from the various parties and dinners he attended with his clients, but a few had been clients at one time or another in his past. Like most wedding receptions, seats were assigned using some planner’s formula to put like-minded people together and encourage conversation.

Anna was talking animatedly with the other guests at their table, something about the newly married couple, Rachel and Inias, and the mountain of gifts they had just finished opening. Michael smiled and nodded, agreeing pleasantly when it was appropriate, but he was uncharacteristically quiet. He watched the people he could see, but there were over three hundred guests between the loft and the terrace, so there was no way to see everyone that was there. Surrounded by beautiful people, men and women alike, wearing their finest designer dresses and suits, showing off for the other guests at the social event of the month, Michael should have been having a fantastic night. 

It wasn’t that he didn’t want to be there, or that he wasn’t enjoying the party. He was just distracted. Despite his best attempts to get the infatuation out of his system, Michael couldn’t stop thinking about the last evening he spent with Crowley. Nearly two weeks had passed since then and Michael hadn’t received any new requests from Crowley. He was more than a little disappointed.

“Are you with us, Michael?” Anna asked, waving a hand in front of his face to catch his attention. Michael thought it was a rather rude way of drawing his focus, but he kept that to himself and smiled apologetically.

“Yeah, I’m sorry,” he replied. “Just got a bit lost in thought, I suppose.”

Anna stood, smoothing the skirt of her dark green, knee-length dress. “Well, if you will excuse me for a moment, I need to visit the powder room,” she told the table. She bent down so that her lips brushed against Michael’s cheek and whispered in his ear. “Meet me in the bathroom in five minutes.” She stood and walked away, hips swaying enticingly as she left. It was almost enough to make Michael forget about Crowley for a moment.

After a few minutes, Michael excused himself from the table and made his way through the crowded loft. The bathrooms were all the way on the other side, near the kitchen. The implication of her request was clear and Michael knew Anna enjoyed public sex—so did he, if he was being honest. He waited by the door to the ladies’ room for a moment, just to see if anyone was coming out before he went in.

Anna leaned against the marble vanity, watching him with brown eyes as he approached her. “Where is your head tonight, Michael?” she asked, pulling him against her by the lapels. 

“My head is right here, right now,” he said, leaning in to capture her mouth with his own in a wet, heated kiss. He wrapped his arms around her waist, parting her soft lips with his tongue and letting the sweet scent of her perfume and the taste of champagne on her tongue distract him from thoughts that constantly, unerringly returned to Crowley.

Anna returned the kiss eagerly, energetically, and her hands roamed across his back as she turned them so Michael was the one leaning back against the counter. There was a playful twinkle in her brown eyes as she broke the kiss. One hand on Michael’s chest held him back as he chased after another kiss. He let out a disappointed, entirely undignified whine, and she winked at him. She lowered herself to her knees, hands trailing down his sides and over his hips. “I think you need a reminder of what you’re here for,” she said, palming his hardening length through his pants.

Stifling a moan, Michael licked his lips, watching as Anna unzipped his pants and pulled his cock out. “Are we gonna do this right here?” he asked, eyes flicking to the door. There were two perfectly good, semi-private stalls right in front of them, but Michael had to admit the idea that someone could walk through that door and see them sent a thrill down his spine. Anna’s pink tongue circled the head of his dick and Michael moaned. “Oh, yeah, we’re doing this right here.”

“Just don’t fuck up my hair,” she said before her lips closed around him. Anna was sloppy, wanton as she sucked him off. Wet, lascivious sounds filled the air and Michael’s fingers gripped the edge of the countertop tightly. She took as much of his cock as she could fit until she was gagging. Her throat tightening around the head as tears sprang to her eyes. Michael was dying to thread his fingers through her long red hair, but he kept his hands on the marble instead. 

“Fuck,” he growled, wondering how a girl like her learned how to suck dick like that. Heat pooled in his gut and his balls tightened. The click of the bathroom door opening distracted him and he glanced over to see an older woman in a lavender dress walking in. She looked shocked, but a second passed and she smiled wryly.

“Ah, I remember those days,” she said, backing out of the room and letting the door swing shut behind her. 

Michael burst out laughing, but then Anna did something with her tongue that made his entire body stutter, and his eyes were locked with hers again. She looked absolutely debauched, cheeks flushed and eyes wide. Her mascara was smearing a bit from the tears that fell as she choked on his cock again. It was hot as hell.

Michael reached out to fist a hand in her hair, but stopped short of actually touching it and closed his hand around empty air instead. Anna held his hips, pushing them back against the countertop as she hollowed her cheeks and sucked hard. “Fuck, Anna,” he gasped, teetering on the edge of release.

Anna swallowed around him, and Michael’s hips bucked forward as he came hard. She worked him through his orgasm without losing a single drop, then tucked his cock away in his pants, zipped him up, and stood with a smile. “Feel better?” she asked, moving around him to look at herself in the mirror.

“Mmhmmm,” Michael replied, still catching his breath. He turned and looked into the mirror himself. His cheeks were flushed and his pupils were dilated. He almost looked like he was high. He grinned and glanced over at Anna.

“Good.” She was fixing her eye makeup. “Hopefully, you’ll be able to keep your attention where it belongs for the rest of the night because that was just the opening act, honey.” She smiled sweetly at him, turned on her heel and walked out.

Michael waited for a moment before following her out the door. The loft was just as crowded as before—unsurprisingly, as they’d actually been in the bathroom for less than ten minutes—but Michael’s mood had changed. He smiled brightly as he waded through the crowd back toward their table. Anna was already sitting. He bent down and said, “I’m going to grab a drink, would you like another glass of champagne?”

“Please,” she said before turning back to whatever conversation was happening.

He made his way over to the bar and ordered a glass of champagne for Anna and Booker’s on the rocks for himself from a tall, ridiculously skinny kid with a mile-wide grin that seemed permanently affixed to his face. The enthusiastic bartender nodded and walked to the other end of the bar. Michael looked around the room while he waited, just taking it all in now that he was feeling slightly less burdened by feelings he hadn’t asked for.

The loft itself was beautifully decorated with large white and lavender blooms and ribbons, translucent white chiffon draped artfully from the ceiling, and nearly pristine white linen tablecloths on every table. It had probably taken hours for the florists to meticulously create the floral centerpieces for each table; they all matched perfectly. The lights were low and warm, setting a lovely mood for an evening reception as the sun dipped below the horizon somewhere beyond the city. Michael thought he should spend some time on the terrace once the sun set and the sky was dark. This high up, the breeze nearly always blew and no matter how long he lived in New York, he never tired of seeing it lit up at night.

Michael looked down toward the end of the bar, searching for the bartender. But instead he saw the last person he expected—or wanted, at that moment—to see. Crowley stood at the table closest to the bar with a drink in one hand and the other resting on the back of an occupied chair. He was well-dressed, as always, in a dark gray tailored Italian suit with a black shirt. Unlike the other times Michael had seen him, Crowley’s tie was loose around his neck, the top two buttons of the shirt undone. He looked comfortable and relaxed.

The occupant of the chair his hand rested on was a man, probably a few years older than Crowley, who looked a little rough around the edges. He wore a nice suit, but it was clearly cheaper than the formal attire of the other guests, and he looked a little uncomfortable. He tugged at his collar and said something that Crowley bent down to hear. Michael’s throat tightened, what was left of his floating orgasmic high dissipating as Crowley squeezed the man’s shoulder and responded to whatever had been said with a soft, affectionate gaze. The whole exchange seemed intimate to Michael and he looked away, though he wasn’t sure if it was because he thought he shouldn’t be looking or because of the jealousy that suddenly reared its head.

The bartender finally returned with the drinks and Michael thanked him politely as he took them and went back to his seat at the table with Anna. He was oblivious to the conversation, staring just as he’d been doing before their little bathroom tryst. But this time, his eyes were unerringly on Crowley and whoever the man with him was. Michael’s feelings were getting away from him, making him wonder who Crowley’s date was. 

Why had he hired Michael in the first place? Crowley clearly had someone that was willing to accompany him to parties and dinners and such. Judging from the way he smiled and laughed with the other man, Crowley enjoyed his company. Did his date know that Crowley had hired Michael and let him fuck him until he couldn’t think clearly? Michael had been so certain that the client appreciation dinner had just been an effort to spend more time with him. It definitely hadn’t been about sex, so what was going on?

Michael knew he was overthinking, but he couldn’t seem to get his mind to slow down. His imagination was running wild, picturing everything from the two men having a romantic candlelight dinner to Crowley fucking his date into the mattress. It was ridiculous and unpleasant. It was also entirely uncalled for. Not only did Michael barely know Crowley, but he was a client. It was just a business transaction, nothing more. Despite what his emotions tried to convince him of.

The rest of the reception seemed to drag on endlessly and Michael never made it out onto the terrace. When the time came to leave, he politely said his farewells and retrieved Anna’s jacket and his from the coat check. He pulled his on and draped Anna’s over her shoulders before they stepped outside and he flagged down a taxi. Anna chattered away as they rode through the downtown streets toward her home; Michael smiled and nodded, pretending to pay attention but he didn’t hear a word she said. He was far too preoccupied, his mood dipping even further now that they were away from the party and people.

The taxi pulled up to the curb in front of Anna’s building, and Michael stepped out and walked around the car to open her door. He offered her a hand and helped her out of the car after she paid the driver. Then she practically dragged him into a kiss in the elevator.

What was wrong with him? 

Anna was beautiful and wanton, never dull, but as Michael’s lips and tongue went through the motions of a kiss, he didn’t feel the usual spark of arousal. It was lackluster at best, and it had nothing to do with Anna. The elevator door slid open and she pulled Michael by his tie to her door, somehow managing to slip the key in and unlock it without ever breaking away from him. Even in the weird emotional state he was in, Michael was impressed. It didn’t take long for them to get to her bedroom and for clothes to start coming off.

His arms were wrapped around Anna, her teeth grazing the flesh of his neck, but Michael couldn’t stop thinking about Crowley. Even as she reached between them to palm his cock through the boxers he still wore, his body refused to respond. She pulled away, green eyes examining his face carefully, but Michael couldn’t bring himself to meet them.

“Michael, are you alright?” she asked, cupping his face in one hand and making him face her. “You’ve been acting strange all night. What’s going on?”

Anna’s concern for him was real; he could tell from the way she looked at him. Hell, Michael had known her nearly as long as Cas and he could read her like a book. He shouldn’t tell her. It was never appropriate to dump his emotional baggage on a client’s doorstep, but the words came out anyway. “I think I’m in love with a client.”

“Oh, honey,” Anna said sympathetically. She took a step away from him, and for the first time in a very very long time, Michael felt exposed and vulnerable. Anna crossed the bedroom to her closet, pulled a plush bathrobe out and tossed it to him.

“I’m sorry. I don’t know what’s wrong with me,” he said as he caught the soft fabric in a fist on instinct. “I know you paid for the whole night. I’ll refund everything but the time we spent at the party.”

Anna shook her head, pulling on another bathrobe and tying it shut to cover her nudity. “Absolutely not. You’re not going home alone in this state. Put that on and come out to the living room, I’ll be in there in a second.” She walked out of the room, leaving Michael more than a little confused, half-naked, and holding a robe he wasn’t sure was big enough to cover anything important.

He stared at the door for a long moment before finally shrugging the soft, plush fabric over his shoulders. It was pale pink and only hung to his mid-thigh but it was warm and comfortable, and somehow seemed like exactly what he needed right that moment. With a sigh, Michael tied the belt around his waist and made his way out to the living room.

Anna sat on the floor, leaning back against the sofa. She had pushed the coffee table closer to the TV so she could sit cross-legged, and she giggled when she looked up at Michael. “I swear I didn’t do that on purpose, but you look adorable.”

He couldn’t help but smile back at her. She held up a glass of red wine and gestured for Michael to come sit on the floor next to her. When he did, Anna handed him his own glass, a pint of Rocky Road, and a spoon. 

“Come on, we’re gonna watch rom-coms, eat ice cream, and drink. And you are going to tell me all about this client.” Anna scooted over until their shoulders were touching and picked up the remote, scrolling through Netflix until she landed on  _ PS I Love You _ . “Oh, this is my favorite movie!”

Michael laughed, the tension in his shoulders releasing as he leaned back against the couch and dug the spoon into his ice cream. He stayed silent as the opening scenes of the movie played, pretending he didn’t have every line of it memorized. “Gerard Butler is hot as hell,” he said finally.

Anna agreed enthusiastically and took a sip of her wine. “So, what about this client?”

Grimacing, Michael hesitated, watching the movie silently a moment longer. “We’ll call him Mark. I haven’t known him for long. I’ve only seen him twice. Which makes this even more insane, honestly.”

“He must be one hell of a guy,” Anna said softly. Neither of them looked at each other; they kept their eyes on the screen and spoke between way-too-big spoonfuls of ice cream and sips of wine.

“Yeah, I don’t know him at all, really. But I think he is.” It was strangely comforting to sit with Anna and watch some other idiot dealing with problems of the heart. Michael had never done anything quite like it before. Sure, he watched action movies with Luke when either of them was in a piss poor mood, but that wasn’t really the same. “He’s really smart. And funny. Not in a stand-up comedian way, or anything, but he’s got a really dry, sarcastic sense of humor.”

Anna laid her head on Michael’s shoulder and listened as he kept talking. He was surprised by how much he had to say and how easy it was to talk to her.

“Mark projects this super confident image.” He paused for another spoonful and tried not to think about how many extra miles he was going to have to run for this indulgence. “But he’s definitely got a soft side. I’m not even sure he realizes it. It’s like no one has ever taken the time to care for him, you know?”

“Hmmm, sounds like someone else I know,” Anna said, gesturing at Michael with her spoon. 

He shook his head. “No, it’s different. I’ve certainly had some rough spots, but I’ve at least always had my brother. I’ve never really been alone.”

“And Mark has?”

“Yeah, I think so.” Michael set his empty ice cream carton on the table and pulled one knee up to his chest. He interlocked his fingers and turned to look at Anna, resting his head against his thigh. “I mean, he isn’t alone now, apparently. I saw him at the reception with some other guy. Seemed like they were together.”

Anna nodded. “That’s rough.” They watched the movie for a while without talking. “You know what isn’t rough?” she asked eventually, gesturing toward Jeffrey Dean Morgan naked on the screen. “That ass. Oh my god.”

Michael shrugged and laughed. “Yeah, it's alright, I guess. Mine’s better, though.”

They didn’t talk about Crowley anymore, and when  _ PS I Love You _ ended, Anna just picked another movie. By the end of the second one, they’d been through two bottles of wine and a long conversation about which Avenger they would rather fuck. Michael felt better, partly because of the alcohol, but mostly because Anna was distracting him. They watched movies until they passed out in the living room.

The hangover Michael rode home with was more than worth it.


End file.
